Allylation of ketones with a ferrocene-based planar chiral lewis acid

Ramez Boshra, Ami Doshi, Frieder Jäkle

Research output: Contribution to journalArticle

28 Scopus citations

Abstract

Flat, like your hand: The heteronuclear bidentate Lewis acid 1,2-Fc(BMeCl)-(SnMe2Cl) is readily resolved into its constituent enantiomers through highly stereoselective complexation with N-methylpseudoephedrine. The resulting planar chiral Lewis acids show optical purities greater than 97 % and, upon conversion to the respective allylborane derivatives (see scheme), rapidly add to ketones with enantiomeric excess of up to 80 %. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)1134-1137
Number of pages4
JournalAngewandte Chemie - International Edition
Volume47
Issue number6
DOIs
StatePublished - Feb 11 2008

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Catalysis

Keywords

  • Allylation
  • Boron
  • Chirality
  • Ferrocene
  • Organoboranes

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